For the first time in Sheriff Alfred Montgomery’s short, scandal-plagued tenure, he’s picked up some defenders who are not on his own payroll—even if their support is less about Montgomery and more about opposing Missouri Attorney General Andrew Bailey.
Montgomery, whose tenure has been defined by a flamboyant chaos involving everything from questionable golf cart purchases to personnel decisions made via golden dice to allegations that he’s not transporting detainees to and from the hospital, now faces a removal petition from Bailey. And that’s led to a sentiment that Montgomery may be a fool, but he’s the city’s fool—though of course elected leaders like Alderman Rasheen Aldridge don’t phrase it exactly that way.
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Aldridge says that his Budget Committee has called Montgomery before them and asked plenty of hard questions on a number of issues—“but I’m not sure if they rise to the level of resignation.”
Aldridge, who spent four years as a state legislator, says that Bailey’s move coming on the heels of the city police going back under the control of a state-controlled board feels like overreach from Jefferson City.
“I think city voters make that kind of decision,” Aldridge says about removing an elected official. “I don’t think we’re at the extreme right now to have the attorney general, who’s trying to use this for political points, to say I took down another Black leader in the city of St Louis.”
He adds, “I heard the AG say something like, ‘We’ll hold every politician accountable.’ What is next? Who is going to get told they got to leave office because the attorney general doesn’t like them?”
Aldridge also sees a racial component. “You see a lot of this happening with [Jefferson City] Republicans trying to control St Louis City, St Louis County, and also Kansas City. It’s not a shock that the majority of those areas are very diverse.”
On Tuesday, Bailey told Montgomery that he had until noon the following day to resign from office, or face removal proceedings. When Montgomery refused to budge, Bailey filed a quo warranto petition seeking to remove Montgomery from office. He alleges Montgomery engaged in nepotism by hiring his half-brother and that he violated his duties in a slew of ways: by unlawfully detaining a jail director, by using deputies to transport his own children to and from school, by refusing to transport detainees to and from jail.
Montgomery’s spokesman has flat-out denied that he hired a family member. His legal advisor, retired Judge David Mason, is adamant that transportation of detainees isn’t under the purview of the sheriff’s office.
It can be difficult to stick up for Montgomery on his own merits. As one City Hall insider put it: “I haven’t seen many elected officials with such an uncanny knack to make the wrong choices as Montgomery. Anthony Weiner? Gary Hart? George Santos?”
But nonetheless, the insider said, while headlines have consistently characterized Montgomery’s actions as desperate, from a different perspective, Bailey’s can seem just as much so. “Is Montgomery desperately fighting to retain his job or is AG Andrew Bailey desperately fighting to remove him?”
In 2023, when Bailey filed his removal petition against then-Circuit Attorney Kim Gardner, the attorney general was greeted as something of a white knight. But a crucial difference is that Gardner was derelict in her role as the city’s top prosecutor. Montgomery is essentially responsible for security at two courthouses.
Also, the grievance against Gardner was that people who killed other people weren’t being prosecuted and were back out on the streets. “There’s a totally different level between the roles and responsibilities of that office compared to the sheriff’s office,” says Aldridge.
Alderman Mike Browning has been alongside Aldridge on the Budget Committee asking Montgomery tough questions about spending. Browning, however, is in favor of Bailey’s removal. “I’m no fan of Andrew Bailey, but this is the legal mechanism by which we can get a sheriff who can do the job,” he says.
He adds a voter recall is technically possible, but it’s “extremely expensive and time consuming” and has to be done within tight timing restrictions. (Browning reached out to SLM not long after this story’s publication to say he looked into the matter more, and voter recalls are only possible in Missouri in third class cities, which St. Louis is not. So a voter recall is in fact not an option.)
Browning points out that the allegations against Montgomery, particularly of financial mismanagement, are well documented. During a Budget Committee hearing, the sheriff asked for more money because, in Browning’s words, “He had blown a $600,000 hole in his budget.” Aldridge notes, however, that the funds, while not wisely spent, did go to items for his department, like badges and vehicles. Gardner misused funds to pay for her personal legal fees.
State Rep. Marty Joe Murray (D-St. Louis) says that he too thinks that Montgomery’s situation is different than Gardner’s, that objections to the former circuit attorney could be attributed more to her exclusion list and over-arching approach to criminal justice reform. A backlash against “defund the police” rhetoric fueled the push against Gardner, Murray texted. “The quo warranto against Sheriff Montgomery is more about exerting control over St. Louis,” he added.
State Senator Karla May, (D-St. Louis) is also among those who have chimed in with a voice against the removal process.
She said in a statement Tuesday that the allegations against Montgomery should be addressed through “transparent and lawful channels, not through threats or political maneuvers designed to bypass the will of the voters.” She added: “The law exists to protect the integrity of elections, not to serve as a weapon for political retribution.”
The sheriff prior to Montgomery, Vernon Betts, had his own rocky tenure. He was accused of, among other things, berating a deputy with racial slurs for not supporting him politically, as well as upbraiding a city resident for calling him as he watched Mulan with his family.
One city politico quips that after Betts, the city had a nine out of ten chance of not picking someone worse. “But this being St. Louis, we found the one.”
Speaking of Betts, it was well known around the courthouse that his brother, Cordell Howard Betts, worked as a deputy during his tenure as sheriff. Hired in 2006, Cordell’s employment predated Betts’ election as sheriff. But, according to Bailey’s removal petition for Montgomery, “The Missouri Constitution explicitly prohibits any public officer from appointing or employing any relative “within the fourth degree, by consanguinity or affinity[.]’”
Bailey did not respond to our question about whether he ever looked into the matter of Betts employing his brother. Nor did he respond to our question about whether he’d be willing to allow Montgomery to roll golden dice to keep his job.
